Princess Diana's Best Looks of All Time

As we prepare for the royal wedding of Prince Harry and Meghan Markle, we have been discussing the fashion icon status of both Meghan as well as Kate Middleton at great length. It was, however, Princess Diana who did it first, challenging the restrictions of royal fashion and style with each and every thing that she wore. Whether it was a dress that was tighter or shorter than the norm, her affinity for non-British designers, or her choice to wear custom creations that were unapologetically modern, she broke boundaries and paved the way for not only her daughters-in-law, but for all the other fashion enthusiasts who strive to do the same. In honor of the OG royal style icon, here are her 20 most memorable looks.

February 1981

To announce her engagement to Prince Charles, Diana chose a simple blue suit and tied-neck blouse. Many look to this outfit when they discuss Kate Middleton and Prince William’s engagement, which they announced while she was wearing a similarly-fashioned blue dress.

July 1981

For her wedding to Prince Charles, Diana wore a custom gown from David and Elizabeth Emanuel. It boasted gigantic puffy sleeves, lace ruffles, and a massive 25-foot train.Dress, David and Elizabeth Emanuel.

November 1981

Though we now know Kate Middleton as the queen of gorgeous coats (and Meghan Markle has been killing the outerwear game as well!), it was Diana who did it first, wearing a colorful fringe coat after officially announcing her first pregnancy.

October 1985

Always the rebellious one, Diana chose to wear an emerald-and-diamond choker around her head, as a tiara. The piece was a gift from the queen, who likely didn’t have this look in mind when she picked the necklace out for the Princess.

May 1988

May 1989

This stunning gown was a true princess moment, as she paired it with the Spencer tiara. A similar style was also crafted of pink silk with a matching jacket, selling at auction for $51,750 after Diana’s death.Dress, Catherine Walker.

March 1993

June 1994

Yes, this dress is the little black dress to end all little black dresses. But the timing was perfect in that she chose to wear it at the same time as a documentary was airing about Prince Charles’ infidelity, ensuring that the next morning’s headlines were almost exclusively about her stunning look and hardly at all about her husband’s wandering eye during their marriage.Dress, Christina Stambolian.

September 1995

Much is discussed about the royals choosing to wear British designers or those of other nations now, but Diana was required at the time to stick exclusively to those based in the UK for economic reasons. After her split, she was often seen straying from the nation, in bold looks like this red Christian Lacroix.Dress, Christian Lacroix.

September 1995

Often favoring designers in the areas she visited, she became a huge fan of the mini sheath dress, showing off a more daring look than she hadn't previously been allowed to while still married to Prince Charles (though she certainly pushed boundaries then, as well!).Dress, Versace.

November 1995

This look was designed specifically for Diana by Gianni Versace with a nod to the last great fashion icon: Jackie O. She was also seen wearing it with a matching pillbox hat, designed by Philip Somerville.
Suit, Versace.